


Loving Restraint

by ADevilsHunger (Dream_tempo)



Category: Teen Wolf (TV)
Genre: Chastity Device, Cock Cages, Exhibitionism, Light Dom/sub, M/M, Masturbation, Orgasm Delay/Denial, Plot What Plot/Porn Without Plot, Prompt Fic, Public Sex, Teacher-Student Relationship, Voyeurism
Language: English
Status: In-Progress
Published: 2014-09-09
Updated: 2016-08-06
Packaged: 2018-02-16 19:00:55
Rating: Explicit
Warnings: Creator Chose Not To Use Archive Warnings
Chapters: 3
Words: 10,174
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/2281062
Author URL: https://archiveofourown.org/users/Dream_tempo/pseuds/ADevilsHunger
Summary: <blockquote class="userstuff">
              <p>The boy may be smart, but there’s never a perfect way to hide an addiction—especially not when it calls to someone else and resonates behind their chest. Derek notices that he uses the restroom every single period they are together. Derek notices that it’s almost always a clear cut ten minutes that he’s away. He notices the tube of hand lotion tucked into Stiles’ back pocket when he goes and how he always reeks of the heavy perfumes when he comes back. The flush high on his cheeks, the sweat glistening just in his hair line, the heaviness of his breath, the scrunched bundle of his boxers above the waistband of his jeans after they were too hastily pulled up—he notices these too.</p><p>Every day, like clockwork, Stiles gets up from his seat, asks for the bathroom pass, and goes into a stall to masturbate. </p><p>AKA the one where Derek is Stiles' high school history teacher and also his secret Dom.</p>
            </blockquote>





	1. Chapter 1

**Author's Note:**

  * For [invisiblebike](https://archiveofourown.org/users/invisiblebike/gifts).



> So I polled my tumblr followers yesterday on how best they'd like me to keep filling their prompts and based on everyone's answers, most of them preferred shorter fills with more frequency. Here's me attempting to do that. :P Hope it still works for you guys! 
> 
> Based on the prompts:  
> 

Stiles Stilinski is an impossible boy to ignore. At least for Derek. The entirety of his student body doesn’t seem to have any problem with the notion, but for Derek it’s like asking him not to breathe. Sure, Stiles is quiet and hides himself in corners of the classroom— swaddled in bulky flannels, beautiful eyes behind thick black frames—but that doesn’t do anything to hide his long, lanky build, the lush pink of his skin. He’s smart and sharp and so, so observant, it almost scares Derek.

Because surely the boy knows.

Surely he can see the hunger in Derek’s eyes when he asks a question and looks to Stiles first for the answer. Surely he can feel the electricity in their skin when Derek “accidentally” skims his fingers over Stiles’ hand as he passes back his paper. Surely he has to know that Derek has touched himself at night, thinking of the two of them together. How could he not?

Derek notices the things Stiles thinks he hides so well, so he doesn’t think it’s so far off to believe Stiles can see through him as well. The boy may be smart, but there’s never a perfect way to hide an addiction—especially not when it calls to someone else and resonates behind their chest. Derek notices that he uses the restroom every single period they are together. Derek notices that it’s almost always a clear cut ten minutes that he’s away. He notices the tube of hand lotion tucked into Stiles’ back pocket when he goes and how he always reeks of the heavy perfumes when he comes back. The flush high on his cheeks, the sweat glistening just in his hair line, the heaviness of his breath, the scrunched bundle of his boxers above the waistband of his jeans after they were too hastily pulled up—he notices these too.

Every day, like clockwork, Stiles gets up from his seat, asks for the bathroom pass, and goes into a stall to masturbate. Judging by the frequency with which he swaps out lotion bottles, it’s more than just in Derek’s class too. He’d be willing to bet the boy unloads with breakfast, lunch, and dinner—a habit he’s let grow into a chronic condition.

Derek finds himself wondering if the sensitive pink skin of his cock chafes, if he would flinch from oversensitivity while Derek kissed it—if his beard would burn excessively. He wonders if Stiles gets off on doing it in public—if he doesn’t even try and hide the wet sounds or his soft moans while he stands over the toilet bowl and fucks into his fist. He almost convinces himself he could leave just a minute after Stiles, sit in the stall next to him, and listen. Maybe if he put his fingers beneath the stall divider, Stiles would get on his knees, let Derek help.

These are the things he thinks while his students do quiet work and he sits at his desk, tries not to touch himself beneath the wood. Stiles sits in the back and fails. Derek can see his furtive glances around the classroom before he digs a palm into his crotch—bucks into his own touch—curls around his own hand and minutely humps against it. Sometimes they catch eyes and Stiles blushes and Derek raises a brow and that hand comes flying back to the top of the desk. Derek smiles.

* * *

 

Derek doesn’t know what possesses him to do it, but somehow he finds himself in a sex shop on a Saturday afternoon. He’d been bored and lonely and horny and thinking of the way Stiles stayed after class the day before to go over a rough draft of a paper. He’d hovered behind Derek, reading his own words behind his teacher’s back. Derek could feel his warm breath on the back of his neck, could smell his sharp, boyish sweat. He nearly jumped out of his skin when Stiles placed a heavy palm on his shoulder as he leaned over to point out sentence structures that were giving him issue.

And now Derek is looking at cock cages, wondering what Stiles’ favorite color might be—if he’d prefer plastic or silicone. He doesn’t even know if the boy would want him, if he wants other men. He doesn’t know, if he tried, if Stiles would reciprocate or if he’d get arrested. But he can’t keep himself from imagining, and so he’s paying for a baby blue chastity device, picking their smallest size because he remembers breaking up a group of boys a few weeks back teasing Stiles in the locker room about his micro-junk.

Derek actually smiles a little at that because he can’t keep himself from thinking it cute—precious. He wonders if Stiles would be shy about that too, if he’d feel fire in his heart at Derek trying to worship the little thing—misinterpret adoration as pity. He thinks that the young boy would, so self-conscious in everything else. But Derek would show him, would love him until he saw. He would suck the whole thing into his cheeks and work the perfect mouthful until Stiles unloaded in his mouth. He’d let the boy fuck the crease of his thigh, the circle of his fist, the channel of his armpit. Derek would let him play however he would like, happy just to be helping.

That’s what he convinces himself he’s doing. He knows the boy has to be raw, can see how he sometimes walks crookedly, picks at the crotch of his jeans tenderly. He’s taking care of a young student that doesn’t know how to himself. If he locks up that pretty, little cock and lets it recuperate, when Stiles orgasms next, it won’t be with that severe edge of pain. Derek will be able to teach him restraint and control. He’ll show him just how sweet delayed gratification can be.

Derek is ready to make him feel loved and wanted and maybe, finally, sated.


	2. Chapter 2

**Summary for the Chapter:**

> He knows this is what the kid needs, what could make his life so much better, and why shouldn't he do his best to make the boy happy, why shouldn't he look after him when everyone else turns a blind eye? So here lies Derek, the only one with eyes loving enough to know.

**Notes for the Chapter:**

> So I finally found the inspiration to make this a series, which I know is something that a lot of people wanted. I don't have too much plotted out just yet, so I don't know where it's going or gonna end, but I hope you're all happy to come along for the ride and that this helps get me out of my slump! 
> 
> Comments are really appreciated and as always, feel free to come talk to me about prior prompts/fic or maybe drop one of your own [on my tumblr](drivenbyadevilshunger.tumblr.com)

It stays in the bottom drawer of Derek's desk for weeks. At checkout, he'd asked for it to be taken out of its packaging and wrapped in something special. The soft, pliant caged had been nestled in a little black box, sat on padded satin along with the lock, but not the keys. A blue bow, iridescent in the right turn of the light and matching the color of the silicone, tied it shut. The package was so pretty, Derek almost forgot the illicitness of its contents.

That was perfect, that was exactly what he needed. This kind of thing could be jarring, depending on just how virginal Stiles was— compared to what Derek thought of him— and he didn't want the first thing for the boy to see being the crude packaging and its marketing of some of their more extreme products. It would be easiest to throw Stiles in the deep end first, but Derek still wanted to be decent about it, still wanted to be the kind of teacher he wished he'd had when he first started submitting.

Looking at the gift sitting in his classroom made him smile, made his chest grow tight and his stomach flutter pleasantly. Stiles was a good kid, quiet to avoid attention from all the other boys that hounded him, but once brought into his comfort, came absolutely _alive._ His dark eyes would glow with interest and his gesturing would become animated, exaggerated. Derek loved to call on him for muddy details, the things students hoped he would skip over, only bringing them up to give Stiles a moment to shine. He always stapled an extra blank page onto the kid's essays for his own hand written comments and thrilled at how often and freely the teenager would stay after class with him to casually talk about inane history facts. Stiles liked to look up the most obscure, the most bizarre things to try and find something Derek had never heard of before, and lived for the chance when he could make Derek the student for once. It was almost like flirting, if that wasn't so wholly inappropriate, that is.

In the erotica shop he'd practically been shaking with his fears, thinking about what his life would be like if he'd have to register as a sex offender, sure he was some kind of pervert. He thought about the people he'd first trusted, how he saw them now, what he wanted to be done to them, and had felt bile rise in his throat. Now though, with it made out to be how he meant it— a gift—he's almost proud of it. Stiles is a different kind of boy than he was, and Derek is a different kind of person than Kate and Jennifer were. He thinks about what sweet relief Stiles will feel with it on, how much more contented he'll be, how pleasured.

He knows this is what the kid needs, what could make his life so much better, and why shouldn't he do his best to make the boy happy, why shouldn't he look after him when everyone else turns a blind eye? His father is the sheriff and Derek knows Stiles is alone in their home for long, long stretches of time, the two of them sometimes passing each other entirely for nigh on a week. The other teachers, old and set in the archaic system of school, ignore his bullying, say it's good for his character. There are little friends to speak of and they seem casual at best, not for lack of Stiles trying—it's painful to watch his desperation—so here lies Derek, the only one with eyes loving enough to know.

Derek watches him during their classes together, seeing the irritation and discomfort as he tries to find a resting position that doesn't chafe, doesn't agitate. And even with all that, he sees how Stiles has to succumb to his own animal need anyway. The boy winces as he gets up to ask for the bathroom pass, holds his long, elegant hands over his crotch, probably assuming he's safe with everyone imagining him having to hold his bladder instead of his erection. They're so careful with his little, spent cocklet and achingly dry balls, tender but shaking with need.

Derek wants to peel them away, kiss the palms, scrape his teeth across the insides of his wrists, suck those deft fingers into his mouth, all the way down to the last knuckle. He wants to stare Stiles in the eyes as he licks between each digit, takes three of them at a time to bob and suck and tongue. Then he'd take the kid by the back of one knee, hook it over his shoulder, still seated at his desk while Stiles stands. He'd push those fingers between his spread legs, between the bottoms of his asscheeks, to where he's soft and pink and hungry.

He'd bite Stiles' fuzzy, thick thighs as he did, nose underneath the loose, warm heft of his balls, burrow his face in the kid's groin, luxuriating in the feel of all that delicate skin, the soft, dense hair, the heady, boyish musk. Stiles would stay soft, trained for it, and Derek would lick at the tacky wetness coming from his tip despite that, as Stiles massaged his own prostate with Derek's guidance.

By the time his student actually gets to the desk, blushing as he asks, like clockwork, to be released, Derek can feel he's made a damp spot in the front of his briefs. He hopes it hasn't soaked to his slacks yet, and clears his throat as he gathers himself, trying not to stare too much at the twitch of Stiles' hands, the little, anxious dance he's doing, how he can practically smell the sex on him. “I'm beginning to think you find my class unbearably dull, Mr. Stilinski.” Derek's voice is rough, but quiet as he rummages through his desk to find the wooden fob for Stiles to take, and he keeps his eyes carefully trained downward, else he might get caught staring. Still, he smirks, and finds himself utterly flirtatious any time they talk.

“Not at all!” Stiles is just quick enough to assure to make Derek believe him, regret actually in his tone. “I never thought history could be so sexy.” Derek's smirk turns into a full on grin, teeth flashing as he looks up at Stiles from under his lashes, adjusting his vest and glasses in a preening way. “Not like that! I meant, you know—“ Stiles squirms even more than he was before, neck and ears flushing a delectable red, belly fluttering with shallow breaths. “You just make it so cool and exciting and it all seems like some Showtime drama.” He outright gropes his crotch at this point, practically humping into his hand and makes a little whine. “C-can I go piss?”

Derek just raises an eyebrow at it all, letting Stiles interpret that how he will, and extends the pass out to him, but not stretching forward. His eyes gleam as Stiles has to make that effort, letting go of himself to lean across the desk, showing off the little tent in his jeans and sliver of his pale torso, his dark treasure trail breaking up the smooth skin. Their fingers brush and Derek can't help himself from rubbing them together, flexing his knuckles to curl them against each other for just a passing second before Stiles withdraws with a jerk. His eyes are wide and his dick twitches. “Better not wet yourself in front of me... while everyone else is watching.” Derek prompts when he doesn't turn to leave immediately, and Stiles tumbles over his feet when he does go, making Derek chuckle and touch himself, just a little, under his desk.

When everyone is back to working silently on their projects, he opens the bottom drawer of his desk and stares at the little, black box, touches its sides. The keys have remained in his breast pocket ever since the purchase, never out of reach. He supposes they should be included in the gift, for Stiles to manage his own issue how he needs, or to present to who he deems worth the responsibility. But Derek is used to the weight of them now, likes feeling the outline of their jagged edges through his vest just to know they're there, comforted. Who could be more responsible about it than his teacher?

* * *

 

Derek leaves the box in Stiles' gym locker with a set of handwritten instructions and his phone number Friday evening, while the boys are out on the lacrosse field and no one will see him sneak into the changing room. For his efforts, he leaves with Stiles' underwear tucked tucked into the groin of his own, and the keys in his breast pocket.

* * *

 

He's at home, just a couple hours later, with cooking shows on quietly in the background, a beer open on his coffee table, and a book in one hand. The other is absentmindedly stroking Stiles' boxers along his naked cock and balls, mixing their musks for Derek to bury his face in before bed, when he decides to do something with all this lethargic lust. For now all it's amounted to has been wandering around his apartment naked the whole night and casually touching himself just to feel the warmth stoke under his skin a little longer.

This is not an unusual weekend night for him. Living in an industrial convert in the busiest part of the city, young and single and lushly sexual, he sometimes puts on cam shows, sometimes puts out personal ads and makes a party of similarly lusty inhabitants. Beacon Hills isn't the biggest town and has a pretty suburban population, but still, there is enough to satisfy his appetites. He fucks cheating dads and bearish truckers passing through more than anything else, but they're just as good as the coked out twinks he used to hang around and much less hassle.

He's run into people he knows on the rare occasion—the most jarring being when Chris Argent sucked him dry in a convenience store glory hole—but the mutually assured destruction that comes with anyone ratting in these scenarios has kept him safe. Being a teacher, he knows he's more at risk than the nurses and deputies and white collar weekend warriors that get wide eyed when they recognize each other, but he tends to be naked when it happens and that's always convincing enough to do it anyway.

His apartment is minimal, though designed, and it definitely speaks to the fact that he doesn't do this job for money. He could lay around all day, like the lecherous whore he is, and just become some living ode to Dionysus, some up and coming fuck boy's art installation about youthful hedonism in an urban setting. Derek had, for a while. When he lived in New York he fed off of all that bullshit, letting people film and photograph him, letting the days blur together as he only lived in drugged out cycles of partying, eating, fucking, and passing out.

For a while he loved that life, loved being one of the shooting stars at the center of it. Virile and beautiful and angry, he was made for the scene and thrived in it, but unlike the others, eventually found himself wanting. This? Now? It too made him happy. Different in just enough ways, the same in just enough ways. He chewed at his lips as he juggled his full balls, loose and warm, he let them tumble over his fingers and bounce in his palm before reaching further back to pet at the bundle of nerves behind it, tangling the tips of his digits with the silken hair fuzzing it.

His phone buzzes with a text and Derek stares at it sidelong for a few, long moments, hands stopped, chest heaving, energy suddenly electric. This would be something entirely new, something he didn't explicitly plan for himself or even really see coming. His ass clenches in anxious excitement when he can finally force himself to bookmark his place, slide from lounging to sitting, and reach to the table for it. Unrecognized number, only three words:

_Who is this?_

Derek's hands shake a little, starting to sweat, but his nipples are hard and he can't stop from cupping his heavy groin before he answers.

_You can call me Dom or Sir. I don't like Master and Daddy is only for when I'm balls deep._

Derek scratches the insides of his thighs and lays back against his couch, feet propped on the coffee table, legs spread as he waits for the response. Stiles' dad is the sheriff. Even if he didn't give his name or get caught placing the box in the kid's locker, this phone number could be traced, but the boy would have to give him up to his father first. Stiles likes him, Derek knows that. The kid is always attentive, laughs at his dry jokes, loves to stay after and talk ad nauseuem about the most inane things. But does he _want_ Derek? Has he just thrown away what could have been a nice, mentoring friendship because he was horny? His phone buzzes.

_Who says I sub? Or even bottom? Maybe I don't even like dick._

Derek can't help his smile, perhaps a little manic, but genuine all the same. The kid is feisty, and it makes Derek hard to think of all the ways he could be broken in. He likes boys that bite back, buck under hand, make their Alpha earn it. He's been that boy and he knows how rewarding it can be, for both parties. He pulls his foreskin back over his wetting cockhead and then slides it forward again, back and forth, just enough to make his balls jerk a couple of times before he replies.

_Don't be coy, your Sir doesn't like it. You're a needy thing, and that's what makes me want you. I know what troubles you, how you tremble for touch. Don't deprive yourself just because you don't want to ask for what you need. It's okay to **yearn** for sex more than other boys understand. _

Derek wonders if Stiles has ever bent the knee for anyone else, if maybe he likes the way those boys tease him, if it's a game. It could be possible— the jocks' own, personal cum dump. He wouldn't put it past those kids. Anything to get their dicks wet. He wonders if he could get in on it, invite them all over to his house to put a restrained Stiles to use. He'd love to watch their little asses shake as they fucked him, pet their reedy bodies as they quaked, sweat dewing across their skin. He'd make them kiss while they spitroasted their peer, get them to want each other too, take their sloppy leavings as they stroked each other, enjoying Stiles' loose, sticky hole.

_How am I supposed to feel better with my dick locked up?_

Derek comes out of his fantasy feeling a little guilty for how far it went— how easily he could access the image of the underage boys he found most attractive— but fully hard now, and milking his long, hanging sack at the remembered filth of it. He doesn't know that he could ever go that far, but the idea of that much depravity has his mouth dry and his muscles tingling. Stiles would probably like that, wouldn't he? Derek whispering these wonderful, terrible things in his ear while he stroked the space behind his balls, plastered to his back. He wonders if he could make the kid shake with his voice soft, but rumbling.

_That's what I'm going to teach you, boy._

Even though Derek wants to immediately follow this up with instructions, wants to start in on what lies ahead, he waits. He lets his last words sit and watches for Stiles to reply with a yes or a no. He needs that explicit permission, needs to be allowed in. He won't pressure, won't take, no matter how desperately he wants. He could never be the person to bring Stiles more hurt than he's already enduring every day. As he waits, breath thin, he scratches lightly at his belly, rolling his hips to rut his ass, knowing no matter the outcome, he needs something tonight to quell what he's let simmer all day.

_Be gentle, Sir._

Derek's hands shake as he reads and rereads the sentence, thinking of Stiles hunched in on himself as he says it, eyes cast down in his shyness, voice soft. The little plea is so sweet, makes Derek's heart clench, and he can't help but soften at it. He'd meant to throw the boy into the deep end, teach him by acting as though they'd both been through this a dozen times, not keep any kiddie gloves on. But perhaps Stiles needs a little more lead up, a little more acclimation before he's ready. Maybe he hasn't been with any of those boys yet.

_I will. Be gentle with yourself. That precious, pink skin needs its tender moments too. Undress yourself, get in bed, make it comfortable._

Derek stands and makes his way to his own bedroom, suddenly needing a smaller space, something more intimate. The large wall of windows to the side, overlooking the streets, no longer seem like just an indulgence of his own voyeurism. They seem to peek straight through his phone and to the vulnerable boy on the other side, and though it's irrational, Derek wants to give him his privacy. He only turns on a bedside lamp as he enters, slowly ascending to his platform bed, covered in dark, silk sheets. He slides against them, into them, dragging them along every inch of his body and humming softly to himself.

The next text is a picture. A twin bed, faded striped sheets in primary colors. A frayed, stained quilt over top of everything. Stiles is beneath them, head cut out of the frame, bedding pulled up to his sternum. The little thatch of thin chest hair is visible, along with his strong collar bones, long throat, strangely sensual beauty marks, and one firm, pink nipple. Derek stares at the image overlong, eyes crawling over every detail, breath loud as he picks up stroking behind his sac again.

_Touch yourself, but don't get hard. Know your skin. Start at your neck and work your way down. Rub your legs together, feel the rise and fall of your stomach as you breathe, notice the curl of your toes and clench of your thighs. Relax, feel good._

Derek takes his own advice as he waits, closing his eyes to roam around his body. It's changed a lot over the years. He's had every type of build, every type of grooming, always following trends or personal interests. It felt mostly like a tool to use, then, set dressing to draw people in and get to what really mattered. He's been beefy enough to make his neck nearly disappear, completely smooth, lithe and twinkish, boyishly hunky, frat boy built, tattooed and tit pierced and even once so thin you could see his ribs.

_I wanna cum._

Derek rolls onto his side as he huffs out a little, disappointed sigh, frowning down at what was, no doubt, a frantically typed message. Stiles is like an overeager puppy, unable to keep himself from being naughty. It's kind of cute, but frustrating enough that Derek would spank him were he there. He's being obtuse and the boy is too smart for that.

_Don't disobey me, boy. I said to stay soft and so you will. Greedy and needy are two different things and I do not find the first endearing. Twist your tit until it stings. Make yourself soft and stay that way._

Derek nuzzles into one of his pillows as he waits, tangling his feet in his blankets and scrolling back to look at the prior picture, imagining what that sweet, pink nub will look like if Stiles obeys. He wonders if they're sensitive, if Stiles has played with them before in his hours of practiced self pleasure. He wants to suckle them until they nearly burn with over-sensitivity, get them puffy and raised, drag his beard across them after and watch the kid squirm as his dick wets from it.

He gets a video. Blurry and too close up and lit like a shaky cam horror movie, but tantalizing all the same. Ragged breathing can be heard over a box fan off to the side and it hitches when long, blunt fingers come into frame. They rub and flick at the pebbled, rosy nipple centered in the frame before pinching it. The camera shakes with readjustment before the fingers twist, lifting the little mound of flesh from his pec and forcing a high pitched, punched sob from just above. The fingers release just to reset, repeating until the nub is reddened and quivering oh so slightly from a pulse.

_Good boy. Leave that sort of touch for when it's needed. Let your boy-clit rest. There are other pleasures to be had._

Derek flips onto his belly, trapping his hard cock between it and the bedding, finding himself pleased with the outcome of this first, little lesson. Punishment is an essential part of this lifestyle. Some mistake it for the purpose, the sole focus, but it is not, at least for him. Punishment is just a necessary tool, something to help guide you to the places your mind must go. It's an aide and should be doled out only when there's a call for it. There could be an entire session without a single instance that was successful and satisfying. He has not had one yet, but he knows this, implicitly.

There's another video, this one shakier than the last, breathing heavier. It slides down Stiles' surprisingly thickly furred belly, rests just below it. One leg is bare, thigh clenched, rubbing against the other. A blanket covers his groin, though it rests low enough to let Derek follow that dark treasure trail to a thick bush. Stiles pushes his free hand between his legs, whines softly, but pushes the thin sheet taut between his legs to show a visible outline of a flaccid dick.

_Get your present. Your dicklet slides into the body of it. Make sure it's tucked snug enough not to slide and chafe, but not smashed inside. Line up the holes, I won't be letting you out to piss. The straps wrap around behind your balls, clasp at the top with your lock. You can squeeze your sack tight for pleasure, or keep it loose for comfort, but choose well, I will not be meting out relief until you have learned your patience._

Derek starts to hump against his mattress, holding himself up on his elbows, pillow clutched in his arms to bury his face or chest in. His ass clenches around the sheets sliding down his back and he spreads his legs to open his cheeks a little more, draw them deeper. He groans softly at the twin sensations behind and in front of him, shameless in his rutting. His balls are drawing tighter, never up to his body for how incredibly low they hang, but the familiar tenseness makes him fuck faster.

The last video is remarkably smooth, the hands behind the phone camera no longer shaking. Stiles is fully naked and the long, sultry expanse of skin has Derek spitting pre and he continues to wildly hump. The boy's body hair alternates only between utterly sparse and dense, but is always easy to spot for the dark color of it. His extremities are pink, so peachy and soft, accentuated by the bit of baby fat that has yet to burn off his boyish frame. Derek had thought it only present in his still, slightly chubby cheeks, but sees it again in the softness of his belly and thickness of his thighs.

He wonders if Stiles' ass is still fat with it, would be round but squishy, erotic to mash with his hands as he fucks against the kid's taint. His legs are sliding together, ankles hooked, and he moans softly as his hands slide slowly up his body. His fingers are long, but too knobby and blunt to be called elegant. They slide from his thighs, card through his pubes, tickle his flanks, twitch at his abused tit, and then rest at his collar bone, making a show of his long throat.

And there, in the middle of it all, is the cage Derek bought him. The teen's dick was as small as he predicted, lending hardly any space between the body of the chastity device and the ring that secures it around his plump, fuzzy scrotum. It looks sweet in its pastel coloring, loving instead of brutal like the chrome ones. As he's examining its fit, seeing how Stiles lightly parts his legs around it, the boy's hand comes back down to gently pet his fingers along the soft outside, tickling his swollen sac before moving back up to jangle at the little, golden lock keeping it closed.

Derek's brows furrow and his buck teeth dig harshly into his bottom lip as his back tenses, his thigh muscles draw taut. He arches his spine as he grinds, hard as he can manage, into his mattress, ass clenched, balls jumping, dick sticky.

Stiles' voice is low, whispering, his lips a smirk at the little tinking noise of the metal. “Thank you, daddy.”

Derek comes.

 

**Notes for the Chapter:**

> Sorry if it there's lots of little errors, this has only been half-edited, and on that note: I'm always looking for beta's so if you're interested, lemme know! I'd love to get in touch and see if we're a fit.


	3. Chapter 3

**Summary for the Chapter:**

> It's the week after Stiles' gets his chastity device and Derek can hardly restrain himself. In fact, he chooses not to.

**Notes for the Chapter:**

> Themes start getting kind of intense this chapter, so watch out for a ramp up of what was going on last time with Derek's past. Also, this is his from his POV, so there's a lot of survivor's guilt and him viewing himself as a terrible, disgusting thing for those reasons. Watch out if that sort of thing is triggering.

It's hard not to look for, the next time that they have class together. Derek has always had to try a little harder than he should to not stare at the beautiful boys under his tutelage, but Stiles has proven his most challenging one to date, and that was before Derek knew what he looked like naked, the childish pattern of his sheets, the decidedly more adult surprise locked round his tender groin. Derek already paid him more attention than he ought to, due to his bright eyes, eager inquisitiveness, and playfully smart mouth-- now the situation was becoming nearly untenable. 

The boy walked in smoother than he has in months-- the awkwardness of his gait something others probably ascribed to his gangliness, but was much more lurid in fact.His large, dexterous hands still hovered in front of his crotch near constantly, but now they were accompanied by a low, interested sizzle behind the teen's skin. Usually Stiles was always squirming in discomfort, near pain, face twitching in the attempt to hold it back. Now he licked his lips, panted softly, and was full of coiled energy.

It had only been a few days, but being as young as he was, Derek knew the refractory period was truly amazing, could see how much Stiles already wanted to abuse his little cock again. So he'd reined Stiles on a tight leash, but still the boy kept heel. He was the sheriff's son, after all, and so something as simple as removing a slim, discreet lock would not be hard for him to do if he really wanted-- through lock pick or bolt cutters or whatever he preferred. But it seemed as though the trust was implicit. He texted his Dom regularly, questioned often but never disobeyed, and Derek could sense the change it was starting to make.

Stiles was more alert, had more freedom to interact, while still being able to sate that need inside of himself. It was addicting to be a part of, even if it was just in secret. Derek couldn't see the outline of the chastity device behind Stiles' jeans, and even though he had multiple pictures of it by now, he couldn't help his desire to see it in person. He had half a mind to sneak into the boy's locker room at a later period, try and glance to see if Stiles would still change publicly even with it on. He could make an excuse for it, one that the boy might even believe, and just the idea was making him thrill. 

He wondered how the other boys would react to seeing it, unable to hold back the kind of fantasies that were all too common as he pleasured himself. The jocks propping Stiles into an easy, open position on one of the low benches, crowing at him as they egged each other on, young bodies reedy and ripe as they take turns fucking his sloppy hole. He wondered if Stiles could come from just that, if he would more than once, what he would smell and taste like if Derek ate him out after.

It's why he decides to show a documentary in class today, unable to focus enough to teach and even then, chubbed up enough throughout the period that the bulge in his pants would be obscene. He keeps his hands under his desk as he gives into temptation and pulls out his phone to text Stiles, hoping the kids don't catch the glow of it as distinct from the projector.

_ You're due for some pleasuring and I'm feeling generous. Find somewhere private and strip for me. You have five minutes. _

He'd told Stiles earlier that he expected to the boy to keep his phone within reaching distance all day, that he didn't care about the restrictions of his schooling. A boy must always be ready to serve. If Stiles isn't paying attention, the day Derek allows his orgasm will be postponed even further and Derek knows he has been itching for one. He'd been promising Stiles a treat if he kept patient, and Derek had intended to wait a full week before any kind of reward, but Stiles was young and new and Derek hungered for him like he had no one before.

He watches with baited breath for Stiles' face to turn away from the screen, and when it does, he smirks at the surprise etched into his features. The boy squirms in his seat for a couple moments, Derek wondering if he'll really disobey, before getting to his feet and scurrying to the front of the room. Derek does his best to play innocent, but he was never very good at it, and he's never been anything less than flirty with Stiles anyway. So when the boy asks for the bathroom pass again, he can't help but raise a single eyebrow.

“Really Stiles? And here I thought I might finally have your attention with this one. Les Blank seemed like your kind of man.” He says it even as he's fishing the wooden fob out of his desk drawers and holds it aloft with utter amusement in his eyes. God he's playing a dangerous game, but damn does it make him feel alive.

Stiles laughs nervously, quietly so no one pays them much mind. As much as Derek is inappropriate, Stiles does nothing to discourage the way they are together. He likes keeping things between them, this strange, intimate place they've ended up-- always visiting Derek behind closed doors, close enough to whisper, leaning into it. Derek knows he's the adult and Stiles is the teenager and so that's no excuse, but he wants it to be as Stiles rubs the back of his neck and chews lightly on his lips.

“I... he is... that was a great choice, but I've got other men that need some attention?” He laughs a little awkwardly at his own joke as he gestures to the 'little guy' behind his zipper with a jut of his chin, reaching out to grab the fob and this time being the one to rub their fingers. There's no doubt the touch is deliberate, slow and firm and lingering, and Derek lets him, bites his lips back, breath thin. He wants to pull Stiles close, into his lap, tell him he's being a tease and nose along the column of his throat. He wants to rub beard burn into that delicate skin and let everyone see this boy is claimed, is wanted.

He can't stop himself from replying, “I'm jealous.” He looks up at Stiles from under his lashes and the boy is blushing profusely, but not shrinking back from him. Instead he seems invigorated by this, actively trying not to make it something even more. This thing that they're doing, it was never innocent, but it's leagues away from that now. They can't see the shore of what their relationship should be. Stiles won't be legal for two years still, but it feels like the natural escalation of their feelings to be together now anyway. They've been dancing around it for over a year, and Derek should feel guilty for wanting a _boy_ the way he does, but—.

They keep eye contact for several long moments before it breaks and Stiles slides away from his desk, heading out the door, glancing back over his shoulder multiple times as he leaves. Derek should do what he always does, should restrain himself to this space of plausible deniability and let the kid go. He shouldn't be doing what he already is allowing himself, should let Stiles discover love and sex at a more natural pace, with other boys his age. But he doesn't want to give this up so easily.

Derek-- he wants even more than what he was planning on, even. He's able to stay seated until he gets a new text. A picture. Stiles is naked, standing in the stall of a toilet in the boy's locker room. He's twisted so Derek is looking over the long, soft slope of his freckled back, spine arched to pop out his ass, which is almost entirely cut out of frame. All Derek gets is the start of his darkly fuzzed crack and the intimation of back dimples. To get the shot, his arm takes up a third of the picture, but it's so worth the long expanse of soft skin, the flex of his shoulders, the vulnerability.

_ Stay turned around. Close your eyes. You'll be severely punished if you disobey. _

_ Leave the lock undone. _

Derek's breathing is heavy enough someone might have thought he just got in from a run and he has to wipe his hands over and over his pants to try and get them dry. He looks out past the placid, bored faces of his students for just a few moments before he does his best to calmly stand, lope to the door, and head out into the halls. The stark contrast of the fluorescent lights to the darkness of his classroom makes his skin itch, makes him swallow hard, but he continues on down his path.

He doesn't pass anyone on his way to the locker rooms, and he doesn't know whether he's grateful for it or not. He wants to be scared off. He wants to be caught. He wants to have more than just twenty minutes for this. His hands shake as he pushes open the door to gym, through to the boys' side, and he presses them hard against his forehead as he wipes the sweat away from his hairline. It reeks in here, like feet and armpits and balls and piss. It makes him hard.

He loves that unfiltered nature of  _ boys _ . He loves that they're just enough kid and just enough man. Petulant and ripe and messy and hungry and gullible and feral. Derek—Derek could make a life of worshiping and breaking them in. He knows there are men that do that, he belonged to some of them not so long ago. They were all just like him, even, just fast forwarded a few years. All of them independently wealthy, undeniably handsome, often with little to no family of their own. They found boys that entertained them both carnally and otherwise and… sponsored their youth. 

If he stayed in New York, he thinks that would have been the natural progression of his life. Derek often wonders if it's a product of his own history, of being taken so young himself and being perpetually lonely afterwards. He wonders if a therapist would tell him it's manifestation of his trauma-- much in the way kids who got beaten would sometimes turn to do the same, how children of addicts would succumb to the same vices as their parents.

In legal terms, Derek was molested, raped, even. A young boy, seduced by his teacher. And now here he is, hard and spitting pre as he's about to do the same. Of course, he doesn't think of himself that way, sees it differently. But maybe that's the delusion of a sick mind. He closes his eyes and shakes at the idea of it, sweating even more profusely now. He makes a whimpering sound as he gropes himself through his clothing, rolls his hips into it, lips quivering as he lets it all in.

His pleasure feels dirty.

He's a kinky son of a bitch and if ever asked, he'd say he only likes sex when it's nasty, but this is different. This feels  _ wrong,  _ not just sordid. And he—he likes that. It's getting him hotter. His stomach is twisting in revulsion and his mouth tastes sour and it's making him so, so hard. He chews his bottom lip as he reaches into his pants to get ahold of himself better, squeezing his balls and playing in the tacky mess at the tip of his dick. He's fucked up, he's so fucked up and god does it make him want to nut all over that little boy's skin.

Derek feels like he has a fever, like his body is trying to alert him to something very wrong, but he just sits in it, even starts to luxuriate. He runs his hands down his sweaty throat, sniffs at the heady musk of his pits, lets his stomach quake as he leaves his dick and balls to hang out of his pants while he stalks over to the line of stalls next to the showers.

There's a pair of feet inside one of them, and when Derek tests the door, it's open. He swings it slowly, letting it creak so Stiles knows he's there, but the boy is good, doesn't turn. He's completely naked, shivering with all that exposed skin, and Derek wants to blanket him with his own, overheated body. He wants them to balance each other out, to fit like puzzle pieces. He steps inside, leaves the door slightly ajar behind them, slides his large hands up Stiles' flanks.

The boy jerks at his first touch, but then relaxes into it, back arching, thighs shaking as he mewls, soft. His skin is so smooth, his flesh still soft by virtue of age. Derek squeezes the little pooch of baby belly he's yet to work into abs, the pout of his chest-- pink tits pointed and hard. He grips his waist tightly, jerks him back by it, curls his fingers into the silky nest of his pubes.  

It’s so simple to press his mouth to the curve of his shoulders, to breathe him in, get lost in it. It’s easy to let go of what’s burning inside him to focus on Stiles instead. The boy is so telegraphed in his wants and needs, unable or unwilling to try and bury them beneath his skin. Derek can read every note, see the threads, knows just where to tug to make it all better. He licks and sucks at the boy’s freckles, rolls their hips together, rumbles softly to let him know he’s appreciated. But he can’t let himself get carried away just yet. 

It takes everything he has to pull away for a moment, and Stiles has been so obedient up till now, but he knows it’s safer if he curbs his lust for just a second of practicality. Stiles whines, and Derek pinches the inside of his thighs very pointedly, until the kid stops squirming. Then he runs his fingers down the silk of his tie, tugs it out of his vest, undoes the knot with short, sharp pulls. 

He drapes it along Stiles’ long expanses of smooth skin before dropping it in front of Stiles’ face, eyes still clenched, and pulls it taut. He presses it to the boy’s throat for a moment, pulling his head back by the force of it, before letting it slip upwards, catching on the jut of his chin, the upturn of his nose, before settling over his eyes. Stiles’ breath hitches and his back quivers, but he doesn’t move to stop Derek as his dom ties it tight behind his head, rubs his shoulders afterwards, pets his caged dicklet. 

“P-please, sir.” Stiles voice is thin and husky, scraping out his throat as he spreads his legs, juts his ass higher. Derek gropes at the rounded globes of it, mashes and pulls them apart and mashes them again, relishing how pliable they are, the adorable, dense fur between them. He rubs his thick fingers in the crevice, chuckling darkly at how Stiles’ thighs shake, cantering on his bare feet like an eager colt. 

Derek pets his hole with his middle digit, letting it stretch far back enough to stroke over Stiles’ taint before coming up to tease at the resistance of his rim. He’s dry, probably never been stretched-- the bud too small and shy to have been tested. Derek had been meaning to milk his prostate here and now, bruise and abuse the little node deep inside him until Stiles was forcefully coming, probably terrified he was wetting himself, what with his cock still completely flaccid and the cum just oozing in a loose fountain instead of the pressured bursts he’s used to. 

But that will have to wait. They don’t have enough time to make it comfortable and Derek would never move to tear the kid, to use pain to take instead of to give. So he teethes at the top of Stiles’ spine, just scraping them there at first, leaving the tingle of their presence, but then nibbling and pressing to gift indents that will stay for hours after. He growls lightly as he does, takes hold of Stiles’ hips again, slides his hard cock between the boy’s thighs. 

He doesn’t even have to give the command for Stiles to tighten his legs around it, to feel him clench and make a channel for Derek to start fucking. His cock is long enough to push through the bottoms of his asscheeks, behind his balls, to brush against the softness of his cage in each thrust, leaving a trail of his precome in his wake. It gets less and less abrasive with every pass, making lewd and lewder noises, getting Derek closer to coming at a hastened pace. 

His balls are heavy and hot between his legs, smacking against the backs of Stiles’ when his thrusts are more forceful, and the boy whimpers every time the meaty smack reverberates against the metal walls surrounding them. Derek bends him further over the toilet in front of them, make him brace himself against the wall so Derek can wrap him in his arms, envelop him completely. 

Derek doesn’t want him to take in anything but the feel of their skin, the smell of their sweat, the sound of their arhythmic breathing, the tang of blood as he bites his own lips to keep from crying out. This moment is just them, free from anything else. This is getting what they need, sating those things curled deep down inside them, the ones they can’t look at in the daylight. 

One of his hands comes up to grip at Stiles’ throat, turn his head by his jaw, while the other snakes down between his legs again, feeling the proof of his submission. Derek plays with his loosely hanging, warm sac, feeling how Stiles is leaking pre-cum out the hole meant for piss. If he leaves it as it is, the boy will get dirty from it, grow rank, unable to clean himself or manage it if he cared. Derek doesn’t know what his personal hygiene was like before this, but he knows most teenage boys tend to throw it by the wayside anyway. Still, the idea of being the one in charge of this, that he could let Stiles squirm in his own mess, knowing the raunch of it would only intensify until everyone knew, it makes his eyelids flutter, his dick spit. 

He wants to do that, wants Stiles to feel how little say he has. He wants to unlock the boy and clean him right now, first with his mouth, greedy and rough, and then with wetnaps, gentle fingers, slow drags. He leans over Stiles’ back thinking about it, rubs their noses together, smiles at the way the boy chuffs, bumps the bridges, carefully headbutts Derek like a pup looking for firmer affection. It’s easy to dole out, pressing into it to drag their lips against each other, loving how Stiles squeaks at the rasp of his beard. 

Derek licks into his mouth before Stiles gets the tempo of their kissing, catches him off guard so he just lets his jaw hang open, lets Derek map the soft insides of his cheeks, the grating pattern of his molars, the roll of his tongue, the ridges of his palette. Stiles moans softly as Derek just  _ tastes him.  _ It’s not a kiss, there’s no reciprocation. Stiles just lets his mouth hang while Derek licks and sucks and bites and even pulls down to nose at. 

His breath smells like salt and butter and cheese from lunch and it’s intoxicating-- rich and boyish and somehow sensual. Stiles licks his nose and then nips it softly, a little confused at Derek pushing it in there after he’d been assaulting it before. Derek just snorts at him, bumps their heads again, tsks at his boy’s impatience. 

Both hands go to the pale hips again and yanks them back on him, makes Stiles yelp as his attention is returned to their grinding. Derek could stay here, like this, for hours. Could luxuriate in their simmered edging until his balls were aching with the need to release. He wants to. But his class will be turning rowdy from his absence at this point, and Stiles may want time to clean before he returns. 

So Derek bites at him again, hard, makes Stiles cry out and writhe as he digs his teeth just enough to make a mark, then sucks and licks at it to soothe the sting. He can’t keep himself from muttering at least  _ one  _ word during this whole session and grits out a feverish, “Mine.” Stiles just shakes and nods his head, lips quivering. 

For that, Derek spins him around again, pushes him to sit, and then yanks him by the backs of his knees so he’s spread out, lounging on the porcelain before Derek. The older man watches his chest heave, his fingers twitch, his balls draw up and his toes clench as he waits for more input, instruction, touch. 

Derek does not give him any as he starts stripping his cock, hard and fast. His foreskin makes sticky noises as he slides it back and forth, raising his arm and placing it behind his head to snuffle and lick at his own pit, rolling his hips in a show that Stiles won’t see, but he feels compelled to put on nonetheless. He grunts as he gets closer to the edge, over and over, like a dumb beast, and can’t keep from inching closer and closer, pressing their legs together, fucking up into his fist. Stiles’ nipples are a flushed, ruddy pink. His mouth is a wreck. His shoulders are savaged. He’s smiling. “Come on me daddy, please.” 

Derek’s vision doesn’t white out, he doesn’t scream in pleasure, his knees don’t even give out, but he does what his boy asks. His cum is thick, musky, and paints the creases of Stiles’ thighs, mats his bush, runs in rivulets down his skin. The boy’s hands are shaky as they feel their way across his body to find it, trace through the mess, and then rub it in. 

Derek decides not to clean him. Stiles seems like he might enjoy the debauchery of it. That cage will have to come off this weekend, it’ll be obscene by then but not in a tell-tale way. His gym teacher will probably just pull him aside to suggest being more thorough in the showers, maybe change his boxers more than whenever he can be bothered. It won’t give anything away, but the humiliation and threat of discovery will be sweet for them both, and it’ll make it mean something when Derek does clean him. It won’t be a strange, preemptive measure that Stiles won’t understand. He’ll see just how attentive and knowledgeable his dom can be. 

Derek spreads his legs and moves forward, straddling Stiles as he puts his dick to Stiles’ lips, mostly soft, hood pulled all the way over and dripping. “Your treat,” he murmurs. Stiles sniffs at it for a second, rubs his face along the soft, thin skin, and then gives little kitten licks to the sticky opening. Derek sighs, plants his hands on the dividers, lets Stiles’ large hands that are disproportionate to the rest of his frame for now, cup his hangers and chub as he feasts. 

The boy purses his lips as he sucks the tip of Derek’s dick into his mouth, running his tongue under the foreskin and around his cockhead to clean him up. He squeezes Derek’s balls in pleasure, curls fingers through his bush, withdraws to nuzzle at his stomach breathe over his wet shaft, nip at his navel. Derek runs his hands through Stiles’ silky hair, pushes his thumb into his mouth to get bitten, gropes at the marks he left. 

But their time is ticking down, and so he has to pull back. He ushers the boy to move, means for him to stand, but Stiles just collapses to his knees, and Derek chuckles at the instinct, shaking his head minutely. He keeps his hand in Stiles’ hair as he groans, turns back to what he’d been meaning, and starts to piss into the pot. He closes his eyes at the relief of it, rolls his head back, but stiffens when he feels Stiles’ lips delicately pressing against his shaft. He’s far back enough not to interrupt the stream, but Derek can hear his rapid, shallow inhales as he takes in the sharp musk of Derek’s urine, so close to his face. 

He hadn’t asked for this, pushed on it. He hadn’t even thought-- but Stiles has one hand clinging to the back of his pants, fingers curled in his belt loops, torso wrapped round the side of his leg, and patiently waits for Derek to finish before licking him clean, not waiting for Derek to shake. The boy hums in pleasure, sucks longer than he needs to, gets inside Derek’s foreskin again to be thorough, and then noses in his pubes as he waits for Derek to process it. 

“Good boy,” he whispers, eyes suddenly watering. “ _ Good boy. _ ” Both his hands are in Stiles’ hair, massaging his scalp as the kid tilts up to show him his face, even though they can’t make eye contact. His mouth is wet and open, breathing shallowly on Derek’s privates, nose burrowing into his bush every few seconds for another sharp inhale. He’s so open, so trusting-- loving even, now that they’re together. 

It takes everything he has to tuck himself away, zip up, usher Stiles to his feet and  kiss the boy’s tangy lips one last time. When he undoes the knot in his tie, lets the blindfold slip away, he half wants the boy to look at him, to know him and break the rules. They’re still facing each other, and Derek brushes his fingers over the subtle indent his patterned tie left on the skin, but Stiles is obedient, and Derek’s hammering heart skips a couple beats. He kisses each eyelid, dry, lingering presses of his lips. 

It’s all he can do to tear himself away and he does his best not to make it crooked as he loops it back around his neck and walks back, knowing he stinks of a nervous sweat, will have the stains of it under his arms, is much later than he intended. But he can’t find it in himself to count it a regret, to say that it was a mistake. His smile is jittery as he slides back into his dark classroom and barks at his students to hush, his hands shaking as he digs for his phone. 

_ You were perfect, baby. Gonna unlock that little cock of yours this weekend, show you how sweet it can be.  _

He doesn’t get a reply before Stiles is stumbling back into the room, hair in a dozen different directions, clothes twisted up, breathing heavy, reeking of cum. He laughs nervously as he hands Derek back the bathroom pass, their fingers brushing all over again. “You take good care of that little man?” Derek asks, a smirk on his face as well as in his voice. 

Stiles rubs the back of his neck, glancing back at his classmates, seeing that they couldn’t care less about the two of them. “You… could say that.” There’s a long pause as they stare at each other, knowing that there’s a great deal unsaid, that they’re aware of just what that is. “He’s in good hands, that’s for sure.” Stiles blushes at how brazen their talks have gotten, even if they’re coded. His hands spasm and jerk before Stiles seems to make the conscious decision to reach for his groin, readjust himself and give a little grope right in front of his favorite professor. 

“Good,” Derek hums, utterly pleased. His lips curl into a little, genuine smile, preening at the confidence in Stiles’ words. “Take your seat, Mr. Stilinski,” he doesn’t say,  _ before I do something untoward.  _ Stiles grins at him, bouncing a little on his feet, not so quick to get away from Derek’s intense gaze as he was before. 

“Hate to see me leave, but love to watch me go?” he quips, eyeing the way Derek is chewing his bottom lip. His teacher snorts, shaking his head. Stiles’ fingers skitter aimlessly on his desk, just for a few seconds more before he turns away, heads to his chair. Derek doesn’t even try not to watch, lost in thought as Stiles rubs at his bites while he finishes the documentary, with as much attention as he can muster. 

After class, he gets a text. 

_ Wear more of that sexy cologne. Want everyone to smell you on more than just my dick after next time.  _

Derek’s already hard again. 

**Notes for the Chapter:**

> I finally decided on a trajectory for this story. Two more chapters left before a hopefully satisfying finish. Thanks so much for sticking with me as I figured this thing out, and lemme know what you guys think!


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